EP1672055B1 - Compositions de detergents et leurs procedes de production - Google Patents

Compositions de detergents et leurs procedes de production Download PDF

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Publication number
EP1672055B1
EP1672055B1 EP04773697A EP04773697A EP1672055B1 EP 1672055 B1 EP1672055 B1 EP 1672055B1 EP 04773697 A EP04773697 A EP 04773697A EP 04773697 A EP04773697 A EP 04773697A EP 1672055 B1 EP1672055 B1 EP 1672055B1
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EP
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Prior art keywords
long
salt
chain acyl
reaction
fatty acid
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German (de)
English (en)
Japanese (ja)
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EP1672055A1 (fr
EP1672055A4 (fr
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Tatsuya c/o Ajinomoto Co. Inc. HATTORI
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Ajinomoto Co Inc
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Ajinomoto Co Inc
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/88—Polyamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/37—Mixtures of compounds all of which are anionic

Definitions

  • the present invention relates to a cleaning composition
  • a cleaning composition comprising, as cleaning components, (A) N-long-chain acyl glycine or a salt thereof, (B) N-long-chain acyl glycylglycine or a salt thereof, and (C) N-long-chain acyl glycylglycylglycine or a salt thereof, and further, in addition thereto, (D) a higher fatty acid or a salt thereof, if desired, at a specific weight ratio, and a method for preparing efficiently the cleaning components.
  • N-long-chain acyl neutral amino acid salt is a kind of N-long-chain acyl amino acid salt, and is used as a cleaning component for various cleaning compositions, since it has an excellent surface active effect and bacteriostatic effect, and has a low irritation to the skin.
  • the N-long-chain acyl neutral amino acid salt is solely used as a cleaning agent
  • the resulting cleaning agent is likely to bring about such problems that it is insufficient in foamability such as lather amount and foam stabilizing property and is lacking in sensory feeling such as smooth feeling and moisture feeling to be provided after cleaning and drying the body or hair.
  • various attempts have been made.
  • an N-long-chain acylalanine similarly, it needs improving in foamability and smooth feeling for sensory feelings, though it provides moisture feeling, particularly after body cleaning.
  • a surfactant such as an N-long-chain acylamino acid
  • a method wherein the surfactant is added with a small amount of an N-long-chain acylalanylalanine salt, in order to provide a cleaning composition which is enhanced in foamability and foam stabilizing property, gives no creaky feeling upon cleaning, has an excellent resistance to hard water, and is excellent in washing-up feeling or wet feeling Japanese Patent No. 3296062 .
  • the method is insufficient in improvement of smooth feeling after body cleaning.
  • a cleaning composition which comprises an N-long-chain acyl neutral amino acid or a salt thereof and will accomplish both foamability such as lather amount and foam stabilizing property and smooth feeling and moisture feeling after drying.
  • U.S. Patent 2880219 discloses a method wherein a fatty acid is reacted with N-methyl taurine or taurine (aminosulfonic acids) to directly amidate.
  • the reaction of the fatty acid with the aminosulfonic acid requires a sever reaction condition of a high temperature of more than 200 °C for a long time.
  • U.S. Patent 3150156 also discloses a preparation method of an acylmetyltaurine salt.
  • various catalysts have been studied, and however, a lowered temperature of below 200°C has been required to achieve a high yield.
  • JP-A-2002-234868 discloses a preparation method of an acyltaurine salt.
  • a metal compound is used as a catalyst to react a fatty acid with a taurine salt, allowing the reaction time to shortern, but the method can not be exempted from a reaction temperature of beyond 190°C, and further, leaves a slight amount of the catalyst in the reaction product.
  • the reaction mixture per se can not be used directly in a final product.
  • the method has a drawback that to increase the reaction rate and to achieve a high conversion rate require an excessive free amino acid to be added in the reaction mixture of the alkali metal amino acid and the fatty acid, resulting in a surplus of the amino acid left after the reaction.
  • the present invention has been made in the light of the aforementioned background art, and an object thereof is to provide a cleaning composition which is used for cleaning to give abundant foams accompanied with smooth feeling and moisture feeling after cleaning and drying. Another object thereof is to provide an efficient and simple method for preparing an N-long-chain acyl glycine or a salt thereof.
  • the smooth feeling means the smoothness felt when hair or body is touched with hand.
  • the moisture feeling means the state of hair which is free from dryness or drying out, or state of skin which feels fresh and soft.
  • the present inventor has made an intensive study to solve the aforementioned problems, and, as a result, found that the following three components, that is, (A) N-long-chain acyl glycine or a salt thereof, (B) N-long-chain acyl glycylglycine or a salt thereof, and (C) N-long-chain acyl glycylglycylglycine or a salt thereof can be mixed at a specific weight ratio to provide a cleaning composition which brings about abundant foams, is excellent in foam stabilizing property, and furnishes a cleaned and dried body or hair with sensory feeling of both smooth feeling and moisture feeling.
  • (D) a higher fatty acid having 8 to 22 carbon atoms or a salt thereof is added to those three components at a particular weight ratio to mix, thereby to provide the cleaning composition with enhanced creamy property in foam quality. Furthermore, the inventor has found that glycine, a long-chain fatty acid, and at least one of an alkaline substance selected from sodium hydroxide and potassium hydroxide are mixed, kept with heating, in an inert gas atmosphere if desired, and cleared continuously of the water produced during the reaction, allowing dehydration condensation reaction to proceed at a relatively low temperature for a relatively short time, resulting in the efficient production of an N-long-chain acyl glycine salt accompanied with no catalyst employed. On these findings has been completed the present invention.
  • the present invention includes the following embodiments:
  • the present invention can provide a cleaning composition which brings abundant foams, has an excellent foam stabilizing property, and furnishes a cleaned or dried body or hair with sensory feeling of both smooth feeling and moisture feeling. Further, it can provide a cleaning composition which is enhanced creamy property in foam quality. Furthermore, it can prepare the defined N-long-chain acyl glycine salt efficiently with no catalyst employed through dehydration condensation reaction which can proceed at a relatively low temperature for a short time. Therefore, it can provide a reaction mixture which can be used directly in a final product.
  • the cleaning composition of the present invention comprising, as cleaning components, three components (A), (B) and (C), or four components, (D) in addition to (A), (B) and (C) will be explained.
  • the acyl group of the components: (A) N-long-chain acyl glycine or a salt thereof, (B) N-long-chain acyl glycylglycine or a salt thereof, and (C) N-long-chain acyl glycylglycylglycine or a salt thereof, which are used in the cleaning composition of the present invention, is a carbon chain which is derivable from a linear or branched alkyl or alkenyl fatty acid having 8 to 22 carbon atoms, and may be a single chain or mixed chains.
  • Preferred examples are octanoyl group, decanoyl group, lauroyl group, myristoyl group, palmitoyl group, stearoyl group, oleoyl group, coconut oil fatty acid acyl group, palm oil fatty acid acyl group, palm kernel oil fatty acid acyl group.
  • Glycine is used as a starting material of the above-mentioned three components: (A), (B) and (C) of the cleaning composition of the present invention.
  • the base as the salt-forming base component which neutralizes the acyl-neutral amino acid, its dipeptide and its tripeptide of the three components: (A), (B), and (C) in the cleaning composition of the present invention to give their respective corresponding salts, may be one usually used and is not particularly limited.
  • Usable examples are inorganic bases typically represented by alkaline metals such as sodium, potassium, and alkaline earth metals such as magnesium, calcium; ammonia and organic bases typically represented by organic amines such as alkanol amine and basic amino acids such as lysine, and arginine. These can be used solely or in the form of a mixture of two or more thereof.
  • the method for preparing the components (A), (B), and (C) in the cleaning composition of the present invention is not particularly limited.
  • the component (A) can be prepared according to a usual method such as the Schotten-Bauman reaction of an acyl glycine with a long-chain fatty acid chloride derivable from a long-chain fatty acid.
  • the component (B) can be prepared according to a reaction such as the Schotten-Bauman reaction of an acid chloride derivable from (A) with glycine.
  • the component (C) can also be prepared according to a reaction such as the Schotten-Bauman reaction of an acid chloride derivable from (B) with glycine.
  • the total content of the three components (A), (B) and (C) to be employed in the cleaning composition of the present invention is within a range of from 5 to 100% by weight. From the viewpoint of achieving a sufficient effect, preferable is from 7 to 95% by weight, more preferable is from 10 to 90% by weight. The total content of less than 5% by weight can not provide sufficient sensory feelings.
  • a weight ratio of the component (A): the component (B): the component (C) in the cleaning composition of the present invention is within a range of 100: (8 to 50): (0.2 to 18). From the viewpoint of achieving a more distinct effect, preferable is 100: (9 to 45): (0.4 to 10), more preferable is 100: (10 to 40): (0.7 to 10), furthermore preferable is 100: (12 to 35): (1 to 10), and particularly preferable is 100: (14 to 25): (1.5 to 5).
  • the acylamino acid (A) which is derivable from glycine having no optical active center, has inherently a property to give smooth feeling after drying, and can be added with the aforementioned given amount of (B), particularly the component (C) to bring about additionally the moisture feeling after drying.
  • Glycine is mentioned from the viewpoint of easy availability and processing and high stability.
  • a higher fatty acid to be blended in the cleaning composition of the present invention can be the same as the linear or branched alkyl or alkenyl fatty acid having 8 to 22 carbon atoms from which the aforementioned long-chain acyl group is derivable.
  • the ratio of less than 30 or more than 400 brings about insufficient creamy property in foam quality.
  • the cleaning composition thus prepared, of the present invention is usable for hair and body, and, can be used, for example, as shampoos, rinsing shampoos, conditioning shampoos, facial cleanser, makeup removers, cleansing foams, cleansing powders, cleansing lotions, cleansing creams, hand soaps, bar soaps, mouth washes, shaving foams, and body shampoos. Among them, it is preferably used for body.
  • component(s) usually used in cleaning compositions such as oil solutions, surfactants, gums, antiseptic agents, fragrance agents, UV absorbents, moisture holding agents, physiologically active components, antioxidants, anti-inflammatory agents, antibacterial agents, antiperspirants, chelating agents, neutralizing agents, and pH regulating agents in those cleaning composition, as far as they do not inhibit the effects of the present invention, according to exemplified uses and dosage forms.
  • the preparing method of the present invention is a preparing method according to claim 5 wherein (a) a long-chain fatty acid, (b) glycine, and (c) one or both of sodium hydroxide and potassium hydroxide are mixed and heated while the water produced during the reaction is removed continuously, thereby to obtain an N-long-chain acylglycine salt.
  • the continuous removal of the water produced means that the water generated by neutralization with an alkaline substance and the water generated by condensation reaction shall be both positively removed.
  • the removal can be achieved by removing together with an inert gas stream, or by removing under reduced pressure.
  • the long-chain fatty acid to be used as one of the starting materials in the preparing method of the present invention is a saturated or unsaturated linear or branched fatty acid having 8 to 22 carbon atoms.
  • this fatty acid can be a fatty acid of one kind, or a so-called mixed fatty acid of two or more kinds of fatty acids.
  • Such a long-chain fatty acid can be the same as the above-mentioned linear or branched alkyl or alkenyl fatty acid having 8 to 22 carbon atoms which has already been explained in connection with the long-chain acyl to be derivable therefrom.
  • saturated linear fatty acids such as octanoic acid, decanoic acid, undecanoic acid, lauric acid, myristic acid, pentadecanoic acid, palmitic acid, stearic acid, and behenic acid; unsaturated linear fatty acids such as oleic acid and linoleic acid; saturated branched fatty acids such as isostearic acid; mixed fatty acids such as coconut oil fatty acid, and palm oil fatty acid.
  • saturated fatty acids are preferable. From the viewpoint of general purpose, particularly preferable are lauric acid, mylistic acid, pentadecanoic acid, palmitic acid, and saturated mixed fatty acids containing these as the main component.
  • Another starting material used in the preparing method of the present invention is glycine, from the viewpoint of excellent sensory of the reaction product.
  • a long-chain fatty acid and a glycine are used at a molar ratio of 1.5 to 4 moles of the long-chain fatty acid per one mole of the neutral amino acid, and can be used preferably at a molar ratio of 1.5 to 3 moles from the viewpoint of cost and excellent sensory feelings of the reaction product. Further, from the viewpoint of improvement in reaction yield, the ratio is more preferably 2 to 3 moles.
  • a surplus of fatty acid exists to liquefy the reaction mixture, but the reaction mixture, which has a small fatty acid content to lack in fluidity, if sufficiently blended before heating, allows the reaction to proceed in a solid state.
  • any one or both of sodium hydroxide and potassium hydroxide can be used.
  • sodium hydroxide is preferable because of high reaction efficiency.
  • the alkaline substance may be used as it is or in the form of an aqueous solution.
  • the alkaline substance is used in a molar ratio of equivalent or more to the neutral amino acid, from the viewpoint of reaction efficiency. No reaction takes place if no alkaline substance is used. On the other hand, a surplus of alkaline substance is used to cause uniform mixing to be difficult. Thus, a preferable molar ratio is 1 to 1.5. Moreover, taking into consideration the step for removing an excess fatty acid directly from the reaction mixture by manipulations such as reduction of pressure, the more preferable molar ratio is 1 to 1.3.
  • the reaction temperature for the dehydration condensation with heating in the preparing method of the present invention is 150 to 190°C, preferably 160 to 180 °C.
  • a temperature of less than 150°C does not allow the reaction to proceed, or needs a lot of time to complete the reaction.
  • a temperature of more than 190°C is not necessary.
  • the reaction is usually completed within 6 hours.
  • a temperature of 160 to 180°C takes about 2 hours to complete the reaction.
  • the water produced during the reaction is removed continuously, as described above.
  • the reaction mixture is preferably put in an atmosphere of an inert gas such as nitrogen, or helium, in order to avoid coloration due to oxidation.
  • an inert gas such as nitrogen, or helium
  • the N-long-chain acyl glycine salt prepared according to the preparing method of the present invention is in the form of the sodium salt and/or the potassium salt in the reaction mixture due to the used alkaline substance.
  • the reaction mixture can be used as it is directly, or after purified, as a cleaning component for various cleaning compositions.
  • the purification method is not particularly limited, and a method conducted generally in this field can be utilized. For example, there is a method wherein the reaction is completed followed by distilling off an excess fatty acid under a reduced pressure, or a method wherein the reaction mixture is neutralized with a mineral acid such as hydrochloric acid or sulfuric acid to obtain the N-long-chain acyl neutral amino acid in the free form, and then an excess fatty acid can be removed.
  • reaction mixture is particularly preferably used directly as a cleaning component for various cleaning compositions, from the viewpoint that the reaction solution can be, as it is, a product accompanied with no waste solution to drain and can provide a cleaning composition which allows abundant foams upon cleaning and gives refreshing feeling and moisture feeling after cleaning, particularly after body cleaning.
  • the cleaning composition wherein such N-long-chain acyl neutral amino acid salt is used as a cleaning component, is usable for hair and body in the same as has been explained above, and can be used, for example, as shampoos, rinsing shampoos, conditioning shampoos, facial cleanser, makeup removers, cleansing foams, cleansing powders, cleansing lotions, cleansing creams, hand soaps, bar soaps, mouth washes, shaving foams, and body shampoos. Among them, it is preferably used for body.
  • various components usually used in cleaning compositions such as oil solutions, surfactants, gums, antiseptic agents, flagrance agents, UV absorbents, moisture holding agents, physiologically active components, antioxidants, anti-inflammatory agents, antibacterial agents, antiperspirants, chelating agents, neutralizing agents, and pH regulating agents, can be of course blended in those cleaning compositions, as far as they do not inhibit the effects of the present invention, according to exemplified uses and dosage forms.
  • Lather amounts in Table 1 were evaluated on the basis of the lather amounts at 1 minute after the mixer agitation (1 minute lather amount), i.e., ⁇ : 285 ml or more, ⁇ : 270 ml or more and less than 285 ml, ⁇ : 255 ml or more and less than 270 ml, and ⁇ : less than 255 ml.
  • Foam stability was evaluated on the basis of foam retaining rate, i.e., ⁇ : 80% or more, ⁇ : 75% or more and less than 80%, ⁇ : 65% or more and less than 75%, and ⁇ : less than 65%.
  • Foam quality and Feelings after dried in the same table were the results obtained by hand washing evaluation by five professional panelists.
  • the evaluation was done by calculating an average value on the basis of the following standards (a) and (b), and an average of 4.5 or more was regarded as very good ( ⁇ ), 3.5 to 4.4 was regarded as good ( ⁇ ), 2.5 to 3.4 was regarded as usual ( ⁇ ), 2.4 or less was regarded as bad ( ⁇ ).
  • the reaction mixture was quantitatively determined by HPLC, regarding the acylated forms, i.e., the lauroylglycine and laurolyglycylglycine, the non-acylated forms, i.e., the glycylglycine and glycyldiketopiperazine, and the unreacted glycine.
  • the reaction efficiency yield of the acylated forms
  • the overall recovering rate of the glycine present in the mixture was 97.1%.
  • Glycine a fatty acid having a varying carbon chain length (different number of carbon atoms) and an alkaline substance shown in the following Table 3 were used to react in the same manner as in Preparation Example 1, except that the fatty acid and the alkaline substance were reacted in their various amounts (in molar ratio to the glycine) and at various reaction temperatures.
  • the results are also shown in the following Table 3. Note that the contents of the dipeptide and the tripeptide were shown as their relative weight values to the acylamino acid (the acylamino acid being assumed to be 100).
  • a solid cleaning composition was prepared according to the formulation shown in the following Table 4.
  • the solid cleaning agent thus obtained was excellent in foamability and evaluated by hand washing to provide performance to give both moisture feeling and smooth feeling.
  • the numerical values in the Table represent a percent by weight.
  • Table 4 Reaction product of Preparation Example 6 35.0 Reaction product of Preparation Example 7 25.0 Sodium N-stearoyl-L-glutamate 15.0 Sodium salt of coconut oil fatty acid 5.0 Cetanol 5.0 Glycerin 5.0 Sodium hydroxide 3.5 EDTA ⁇ 2Na 0.2 Titanium oxide 0.1 Methylparaben 0.1 Water remainder Total 100.0
  • Cleaning compositions including shampoos, rinsing shampoos, conditioning shampoos, facial cleanser, makeup removers, cleansing foams, cleansing powders, cleansing lotions, cleansing creams, hand soaps, bar soaps, mouth washes, shaving foams, and body shampoos, which can provide abundant foams, are excellent in foam stabilizing property, and allow sensory feelings of both smooth feeling and moisture feeling after cleaning and drying a body or hair, can be provided.

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  • Cosmetics (AREA)

Abstract

L'invention concerne une composition de détergent contenant (A) un acide aminé neutre N-(acyle à chaîne longue) ou un sel de celui-ci, (B) un dipeptide d'acide aminé neutre N-(acyle à chaîne longue) ou un sel de celui-ci, et (C) un tripeptide d'acide aminé neutre N-(acyle à chaîne longue) à un rapport pondéral spécifique et laquelle présente une excellente capacité de moussage et de rétention de mousse et est utilisable pour laver le corps ou les cheveux de manière à les rendre non gras et les hydrater lors du séchage; une composition de détergent laquelle contient (D) un acide gras supérieur selon un rapport pondéral spécifique en plus des trois constituants précités et présente une mousse à l'aspect crémeux amélioré; ainsi qu'un procédé de production d'acides aminés neutre N-(acyle à chaîne longue) ou de sels de ceux-ci, lequel consiste à mélanger un acide aminé neutre avec un acide gras à chaîne longue ainsi qu'au moins une substance alcaline choisie entre l'hydroxyde de sodium et l'hydroxyde de potassium, et à garder le mélange obtenu chauffé, si nécessaire, dans une atmosphère de gaz inerte, tout en éliminant de façon continue l'eau formée par la réaction, lequel procédé permet une progression de la condensation de déshydratation à une température relativement basse en un temps court et permet la production efficace d'acides aminés neutres N-(acyle à chaîne longue) ou de sels de ceux-ci sans aucun catalyseur.

Claims (10)

  1. Composition de nettoyage comprenant 5 à 100 % en poids d'un mélange des composants suivants (A), (B) et (C), le rapport en poids de (A) sur (B) sur (C) dans ledit mélange se trouvant dans la plage de 100 : (8 à 50) : (0,2 à 18) :
    (A) N-acyl glycine à longue chaîne ou un sel de celle-ci ;
    (B) N-acyl glycylglycine à longue chaîne ou un sel de celle-ci ;
    (C) N-acyl glycylglycine à longue chaîne ou un sel de celle-ci ;
    dans laquelle ledit groupe acyle à longue chaîne est l'une, ou un mélange, de chaînes carbonées pouvant être dérivées d'un acide gras alkyle ou alcényle linéaire ou ramifié comportant de 8 à 22 atomes de carbone.
  2. Composition de nettoyage selon la revendication 1, dans laquelle le rapport en poids des composants est (A) : (B) : (C) = 100 : (9 à 45) : (0,4 à 10).
  3. Composition de nettoyage selon la revendication 1 ou 2, qui comprend en outre comme composant de nettoyage, (D) un acide gras supérieur comportant de 8 à 22 atomes de carbone ou un sel de celui-ci.
  4. Composition de nettoyage selon l'une quelconque des revendications 1 à 3, pour une utilisation dans l'hygiène corporelle.
  5. Procédé de préparation d'un sel de N-acyl glycine à longe chaîne, qui comprend le mélange (a) d'un acide gras linéaire ou ramifié saturé ou insaturé comportant de 8 à 22 atomes de carbone, (b) de la glycine et (c) au moins l'une d'une substance alcaline choisie parmi l'hydroxyde de sodium et l'hydroxyde de potassium, le rapport molaire de (a) sur (b) étant dans la plage de 1,5 à 4 : 1, et en soumettant le mélange à une réaction de condensation par déshydratation thermique en chauffant à une température maintenue de 150 à 190 °C tout en retirant en continu l'eau produite pendant la réaction.
  6. Procédé selon la revendication 5, dans lequel la substance alcaline est utilisée sous la forme d'une solution aqueuse.
  7. Procédé de préparation d'un sel de N-acyl glycine à longue chaîne selon la revendication 5 ou 6, dans lequel ladite réaction de condensation par déshydratation thermique est réalisée dans une atmosphère de gaz inerte.
  8. Procédé de préparation d'un sel de N-glycine à longue chaîne selon l'une quelconque des revendications 5 à 7, dans lequel ladite substance alcaline est l'hydroxyde de potassium.
  9. Composition de nettoyage comprenant, comme composant de nettoyage, un sel de N-acyl glycine à longue chaîne préparé par le procédé selon l'une quelconque des revendications 5 à 8.
  10. Composition de nettoyage comprenant, comme composant de nettoyage, le mélange de réaction en soi d'un sel de N-acyl glycine à longue chaîne préparé par le procédé selon l'une quelconque des revendications 5 à 8.
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Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9616011B2 (en) 2005-04-27 2017-04-11 The Procter & Gamble Company Personal care compositions
US20070020220A1 (en) * 2005-04-27 2007-01-25 Procter & Gamble Personal care compositions
DE102006038853A1 (de) 2006-08-18 2008-02-21 Clariant International Limited Verfahren zur Herstellung von Acylglycinaten mittels Direktoxidation
DE102007055265A1 (de) 2007-11-20 2009-05-28 Clariant International Ltd. Verfahren zur Herstellung von Acylglycinaten
DE102008003825A1 (de) 2008-01-10 2009-07-16 Clariant International Ltd. Verfahren zur Herstellung von Acylglycinaten mittels Direktoxidation
EP3795669B1 (fr) * 2009-06-29 2023-10-25 Inolex Investment Corporation Émulsifiants cationiques dérivés non pétrochimiques qui sont des esters d'acides aminés neutralisés et compositions et procédés associés
JP5915647B2 (ja) * 2011-04-28 2016-05-11 味の素株式会社 洗浄剤組成物
US8981134B2 (en) * 2011-07-28 2015-03-17 Conopco, Inc. Amino acid salt containing compositions
US8853447B2 (en) 2011-07-28 2014-10-07 Conopco, Inc. General method for preparing fatty acyl amido based surfactants
US20130029899A1 (en) * 2011-07-28 2013-01-31 Conopco, Inc., D/B/A Unilever Concentrated fatty acyl amido surfactant compositions
US8853433B2 (en) 2011-07-28 2014-10-07 Conopco, Inc. General method for preparing fatty acyl amido based surfactants
US8658589B2 (en) * 2011-07-28 2014-02-25 Conopco, Inc. Fatty acyl amido based surfactant concentrates
US8653018B2 (en) * 2011-07-28 2014-02-18 Conopco, Inc. Fatty acyl amido based surfactant concentrates
US8822711B2 (en) * 2011-07-28 2014-09-02 Conopco, Inc. Method for preparing fatty acyl amido carboxylic acid based surfactants
US8697897B2 (en) * 2011-07-28 2014-04-15 Conopco, Inc. Method for preparing fatty acyl amido carboxylic acid based surfactants
JP6360437B2 (ja) * 2011-12-20 2018-07-18 ユニリーバー・ナームローゼ・ベンノートシヤープ アミノペプチド混合物を含む保湿組成物
WO2014008103A1 (fr) 2012-07-03 2014-01-09 Stepan Company Procédé de préparation de sels d'acides aminés n-acylés
JP6156384B2 (ja) 2012-09-24 2017-07-05 味の素株式会社 スルホン酸塩型界面活性剤および／または硫酸塩型アニオン界面活性剤、ならびに複素環化合物を含む洗浄剤組成物
JP6011999B2 (ja) * 2013-01-21 2016-10-25 味の素株式会社 アミノ酸イオン液体を用いたｎ−アシルアミノ酸又はｎ−アシルペプチドの製造方法
MX2015017533A (es) 2013-07-05 2016-08-08 Akzo Nobel Chemicals Int Bv Sintesis de tensioactivos anionicos novedosos y su uso como recolectores en flotacion por espuma de minerales no sulfurosos.
SG11201600835RA (en) 2013-08-19 2016-03-30 Stepan Co Process for preparing n-acyl amino acid salts
EP3064487B1 (fr) * 2013-10-31 2020-04-29 Ajinomoto Co., Inc. Solution aqueuse contenant un acide aminé n-acyle à chaîne longue acide et/ou un sel correspondant, et son procédé de production
DE102015212507A1 (de) 2015-07-03 2017-01-05 Clariant International Ltd. Verfahren zur Synthese von aliphatischen und aromatischen Amiden
KR101880791B1 (ko) * 2015-10-08 2018-07-20 주식회사 엘지생활건강 아실 글리시네이트 또는 이의 염의 합성 방법 및 이를 사용한 인체 세정제 조성물
EP3478655B1 (fr) 2016-06-29 2020-09-30 Evonik Operations GmbH Procédé de production de tensioactifs
FR3066195B1 (fr) 2017-05-12 2019-06-07 Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic Procede de synthese d'un compose n-acyle sans utiliser de solvant organique ni de chlorure d'acide
FR3066194B1 (fr) * 2017-05-12 2020-01-31 Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic Procede de synthese d'aminoacides n-acyles sans utiliser de solvants ni de chlorure d'acide
WO2018216672A1 (fr) * 2017-05-23 2018-11-29 味の素株式会社 Composition
EP3805249A4 (fr) 2018-06-04 2022-04-27 Suzhou Oulit Biopharm Co., Ltd. Nouveau polymère d'acide aminé supramoléculaire auto-assemblé, son procédé de préparation et son utilisation
JP7121278B2 (ja) * 2018-10-24 2022-08-18 日油株式会社 洗浄剤組成物
EP3992175A4 (fr) * 2019-06-27 2023-07-26 Ajinomoto Co., Inc. Procédé de production d'une composition de cristaux de n epsilon-acylidine à longue chaîne et composition contenant lesdits cristaux
KR102464655B1 (ko) * 2020-12-31 2022-11-07 노승호 알라닌계 계면활성제 조성물 및 이를 포함하는 인체 세정용 조성물
BR112024001179A2 (pt) 2021-07-23 2024-04-30 Suzhou Oulit Biopharm Co Ltd Aminoácido supramolecular ou sal do mesmo, e método de preparação do mesmo e aplicação do mesmo
CN114262276A (zh) * 2021-12-28 2022-04-01 赞宇科技集团股份有限公司 一种脂肪酸直接合成脂肪酰基丙氨酸盐的方法

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL95122C (fr) * 1954-11-22
US3150156A (en) * 1959-08-04 1964-09-22 Lever Brothers Ltd Catalytic process for preparing nu-acyl taurates
NL7100453A (fr) * 1970-01-30 1971-08-03
JPS5242777B2 (fr) * 1971-10-28 1977-10-26
US3985722A (en) * 1973-12-12 1976-10-12 Ajinomoto Co., Inc. Process for preparing N-higher aliphatic acyl derivatives of amino acids, peptides or proteins
JP2876173B2 (ja) * 1991-09-25 1999-03-31 花王株式会社 洗浄剤組成物
GB2259703B (en) * 1991-08-26 1995-01-04 Kao Corp N-(N'-long chain acyl-ß-alanyl)-ß-alanine or its salt and detergent composition containing the same
JP2969397B2 (ja) * 1991-09-10 1999-11-02 花王株式会社 Ｎ−長鎖アシル−β−アラニンの製造方法
JP2990624B2 (ja) * 1991-10-21 1999-12-13 味の素株式会社 油溶性ｎ−長鎖アシル中性アミノ酸エステル及びそれらを含む香粧品及び外用医薬基剤
EP0648833B1 (fr) * 1993-03-30 1999-12-29 Ajinomoto Co., Inc. Composition detergente
FR2705673B1 (fr) * 1993-05-25 1995-07-28 Givaudan Lavirotte Compositions comportant des dérivés d'acides aminés, leurs procédés de préparation et leurs utilisations.
JPH0762399A (ja) * 1993-08-26 1995-03-07 Lion Corp 粒状洗浄剤組成物
US5710295A (en) * 1995-06-06 1998-01-20 Hampshire Chemical Corp. Preparation of alkali metal acyl amino acids
JPH0987666A (ja) * 1995-09-26 1997-03-31 Mitsui Toatsu Chem Inc 洗浄剤組成物
US5578557A (en) * 1996-04-01 1996-11-26 Lyondell Petrochemical Company Food grade compressor oil
DE69723375T3 (de) * 1996-08-30 2012-12-20 Ajinomoto Co., Inc. Waschmittelzusammensetzung
JPH1081656A (ja) * 1996-09-06 1998-03-31 Ajinomoto Co Inc Ｎ−長鎖アシル酸性アミノ酸またはその塩の製造法
TW502011B (en) * 1997-02-05 2002-09-11 Ajinomoto Kk Process for producing n-long-chain acyl acidic amino acids or salts thereof
US6703517B2 (en) * 2001-11-26 2004-03-09 Ajinomoto Co., Inc. Method for preparing N-long chain acyl neutral amino acid

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JP4771134B2 (ja) 2011-09-14
US20060239952A1 (en) 2006-10-26
ES2313068T3 (es) 2009-03-01
EP1672055A1 (fr) 2006-06-21
BRPI0414953A (pt) 2006-11-07
WO2005033255A1 (fr) 2005-04-14
CN1856565A (zh) 2006-11-01
EP1672055A4 (fr) 2006-12-13
JPWO2005033255A1 (ja) 2006-12-14
CN100448968C (zh) 2009-01-07
BRPI0414953B1 (pt) 2016-10-25
DE602004016873D1 (de) 2008-11-13

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